Acetic Anhydride → Methyl 2-acetoxy-5-benzylideneaminobenzoate
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([O:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:22])[CH3:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 2-hydroxy-5-benzylideneaminobenzoate (23.5 g, 92.2 mmole) was dissolved in pyridine (50 ml) and acetic anhydride (11 ml) was added after which the reaction mixture was left at room temperature for 48 hours and evaporated to dryness, in vacuo. The remaining material was recrystallized from hexane to give the title compound (13.4 g, 49%), m.p. 101°-103° C. Found (Calc. for C17H15NO4) C 68.57 (68.69), H 4.98 (5.05) N 4.80 (4.71).